Sodium Bicarbonate → 2-(6-chloro-3-(2-chloroethyl)pyridazin-4-yl)-4-fluoro-1H-indole

HRID 595710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595710
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]=[CH2:9])=[C:4]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([F:19])[CH:15]=[CH:14][CH:13]=3)[CH:3]=1.C([O-])(O)=O.[Na+].[ClH:25].O1CCOCC1>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][CH2:9][Cl:25])=[C:4]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([F:19])[CH:15]=[CH:14][CH:13]=3)[CH:3]=1

Komponenten

4

Edukt 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 903335012-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole

Produkt 1

HCID 903339492-(6-chloro-3-(2-chloroethyl)pyridazin-4-yl)-4-fluoro-1H-indoleAusbeute 66 %

Versuchsvorschrift

A solution of 2-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole (80 mg, 0.29 mmol) in HCl-dioxane (5 mL) was stirred at 50° C. After 15 minutes, NaHCO3 (a.q) was added. The mixture was extracted with DCM. The organic phase was dried over Na2SO4. After being concentrated in vacuo, the residue was purified by prep-TLC (DCM) to give the product of 2-(6-chloro-3-(2-chloroethyl)pyridazin-4-yl)-4-fluoro-1H-indole (60 mg, yield: 66%). 1H-NMR (CDCl3, 400 MHz) δ 9.04 (s, 1H), 7.63 (s, 1H), 7.28˜7.31 (m, 1H), 7.22˜7.26 (m, 1H), 6.99 (d, J=1.6 Hz, 1H), 6.84˜6.93 (m, 1H), 4.24 (t, J=6.4 Hz, 2H), 3.66 (t, J=6.5 Hz, 2H). MS (M+H)+: 310/312.

Aufarbeitung

  1. extractionThe mixture was extracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationAfter being concentrated in vacuo
  4. customthe residue was purified by prep-TLC (DCM)

Quellen und Nachweise

ORD-Eintrag
ord-93aca5ad1a7b42b9bb3567a0b669f93d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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